Photophysical, photochemical, and tumor-selectivity properties of bromine derivatives of rhodamine-123

Photochemistry and Photobiology

Volumn 81, Issue 6, 2005, Pages 1430-1438

  Lacerda, Silvia H D ^a   Abraham, Bindu ^a   Stringfellow, Thomas C ^b   Indig, Guilherme L ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; CRYSTAL VIOLET; DRUG DERIVATIVE; ETHYL VIOLET; FLUORESCENT DYE; FUCHSINE; RHODAMINE 123;

ANIMAL; ARTICLE; CELL CULTURE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; CYTOLOGY; DRUG EFFECT; DRUG SCREENING; FEMALE; HUMAN; KIDNEY; LIGHT; METHODOLOGY; MITOCHONDRION; PATHOLOGY; PHOTOCHEMOTHERAPY; PHYSIOLOGY; RADIATION EXPOSURE; SARCOMA; SPECTROSCOPY; UTERUS CANCER;

ANIMALS; BROMINE; CELL PROLIFERATION; CELLS, CULTURED; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; FLUORESCENT DYES; GENTIAN VIOLET; HUMANS; KIDNEY; LIGHT; MITOCHONDRIA; MOLECULAR STRUCTURE; PHOTOCHEMOTHERAPY; RHODAMINE 123; ROSANILINE DYES; SARCOMA; SPECTRUM ANALYSIS; TUMOR CELLS, CULTURED; UTERINE NEOPLASMS;

CERCOPITHECUS AETHIOPS;

EID: 29844455439     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/2005-08-05-RA-639     Document Type: Article

References (38)

1. Chen, L. B. (1988) Mitochondrial membrane potential in living cells. Ann. Rev. Cell Biol. 4, 155-181.
2. Chen, L. B. (1989) Fluorescent labeling of mitochondria. Methods Cell Biol. 29, 103-123.
3. Davis, S., M. J. Weiss, J. R. Wong, T. J. Lampidis and L. B. Chen (1985) Mitochondrial and plasma membrane potentials cause unusual accumulation and retention of rhodamine-123 by human breast adenocarcinoma-derived MCF-7 cells. J. Biol. Chem. 260, 13844-13850.
4. Morgan, J. and A. R. Oseroff (2001) Mitochondria-based anti-cancer therapy. Adv. Drug Deliv. Rev. 49, 71-86.
5. Oseroff, A. R., D. Ohuoha, G. Ara, D. McAuliffe, J. Foley and L. Cincotta (1986) Intramitochondrial dyes allow selective in vitro photolysis of carcinoma cells. Proc. Natl. Acad. Sci. U S A 83, 9729-9733.
6. Koya, K., Y. Li, H. Wang, T. Ukai, N. Tatsuta, M. Kawakami, T. Shishido and L. B. Chen (1996) MKT-077, a novel rhodacyanine dye in clinical trials, exhibits anticarcinoma activity in preclinical studies based on selective mitochondrial accumulation. Cancer Res. 56, 538-543.
7. Bernal, S. D., T. J. Lampidis, R. M. McIssac and L. B. Chen (1983) Anticarcinoma activity in vivo of rhodamine-123, a mitochondrial-specific dye. Science 222, 169-172.
8. Bernal, S. D., T. J. Lampidis, I. C. Summerhayes and L. B. Chen (1982) Rhodamine-123 selectively reduces clonal growth of carcinoma cells in vitro. Science 218, 1117-1119.
9. Indig, G. L., G. S. Anderson, M. G. Nichols, J. A. Bartlett, W. S. Mellon and F. Sieber (2000) Effect of molecular structure on the performance of triarylmethane dyes as therapeutic agents for photochemical purging of autologous bone marrow grafts from residual tumor cells. J. Pharm. Sci. 89, 88-99.
10. Kandela, I. K., J. A. Bartlett and G. L. Indig (2002) Effect of molecular structure on the selective phototoxicity of triarylmethane dyes towards tumor cells. Photochem. Photobiol. Sci. 1, 309-314.
11. Kandela, I. K., W. Lee and G. L. Indig (2003) Effect of the lipophilic/hydrophilic character of cationic triarylmethane dyes on their selective phototoxicity toward tumor cells. Biotech. Histochem. 78, 157-169.
12. Pal, P., H. Zeng, G. Durocher, D. Girard, T. Li, A. K. Gupta, R. Giasson, L. Blanchard, L. Gaboury, A. Balassy, C. Turmel, A. Laperriere and L. Villeneuve (1996) Phototoxicity of some bromine-substituted rhodamine dyes: synthesis, photophysical properties and application as photosensitizers. Photochem. Photobiol. 63, 161-168.
13. Fang, T. S., J. Lin, R. Schneider, T. Yamada and L. A. Singer (1982) Studies on triplet-singlet energy transfer with 1,3-dibromo-9,10-bis- [phenylethynyl]-antracene. Chem. Phys. Lett. 92, 283-287.
14. Leo, A., C. Hansch and D. Elkins (1971) Partition coefficients and their uses. Chem. Rev. 71, 525-616.
15. Bartlett, J. A. and G. L. Indig (1999) Effect of self-association and protein binding on the photochemical reactivity of triarylmethanes: implications of noncovalent interactions on the competition between photosensitization mechanisms type I and type II. Photochem. Photobiol. 70, 490-498.
16. Moses, F. G., R. S. H. Liu and B. M. Monroe (1969) The merry-go-round quantum yield apparatus. Mol. Photochem. 1, 245-249.
17. 99mTc]hexakis(2- methoxyisobutylisonitrile). J. Med. Chem. 41, 2111-2117.
18. Perry, S. W., L. G. Epstein and H. A. Gelbart (1997) Simultaneous in situ detection of apoptosis and necrosis in monolayer cultures by TUNEL and trypan blue staining. BioTechniques 22, 1102-1106.
19. Lewis, L. M. and G. L. Indig (2000) Solvent effects on the spectroscopic properties of triarylmethane dyes. Dyes Pigments 46, 145-154.
20. Kamlet, M. J., J. L. M. Abboud, M. H. Abraham and R. W. Taft (1983) Linear solvation energy relationships, 23: a comprehensive collection of the solvatochromic parameters Π*, α and β and some methods for simplifying the generalized solvatochromic equation. J. Org. Chem. 48, 2877-2887.
21. Lewis, L. M. and G. L. Indig (2001) Photonuclease activity of mitochondrial triarylmethane photosensitizers. Pharm. Pharmacol. Lett. 11, 22-25.
22. Lewis, L. M. and G. L. Indig (2002) Effect of dye aggregation on triarylmethane-mediated photoinduced damage of hexokinase and DNA. J. Photochem. Photobiol. B Biol. 67, 139-148.
23. Aguiresacona, I. U., F. L. Arbeloa and I. L. Arbeloa (1989) Spectroscopic and thermodynamic study on the aggregation of rhodamines in solution - solvent effect. J. Chem. Educ. 66, 866-869.
24. Turro, N. J. (1978) Modern Molecular Photochemistry. Benjamin/ Cummings, Menlo Park, CA.
25. Summerhayes, I. C., T. J. Lampidis, S. D. Bernal, J. J. Nadakavukaren, K. K. Nadakavukaren, E. L. Shepherd and L. B. Chen (1982) Unusual retention of rhodamine-123 by mitochondria in muscle and carcinoma cells. Proc. Natl. Acad. Sci. U S A 79, 5292-5296.
26. +2-dependent and caspase-3-independent apoptosis caused by damage in Golgi apparatus due to 2,4,5,7-tetrabromorhodamine 123 bromide-induced photodynamic effects. Photochem. Photobiol. 78, 241-247.
27. Villeneuve, L. (1999) Ex vivo photodynamic purging in chronic myelogenous leukaemia and other neoplasias with rhodamine derivatives. Biotechnol. Appl. Biochem. 30, 1-17.
28. Brasseur, N., I. Menard, A. Forget, R. El Jastimi, R. Hamel, N. A. Molfino and J. E. van Lier (2000) Eradication of multiple myeloma and breast cancer cells by TH9402-mediated photodynamic therapy: implication for clinical ex vivo purging of autologous stem cell transplants. Photochem. Photobiol. 72, 780-787.
29. Wadwa, K., S. Smith and A. R. Oseroff (1988) Cationic triarylmethane photosensitizers for selective photochemotherapy: Victoria blue R, Victoria blue BO and malachite green. In Advances in Photochemistry, Proc. SPIE Vol. 997 (Edited by T. Hasan), pp. 154-161, The International Society for Optical Engineering, Bellingham, WA.
30. Rashid, F. and R. W. Horobin (1990) Interaction of molecular probes with living cells and tissues, part 2. Histochemistry 94, 303-308.
31. Baptista, M. S. and G. L. Indig (1998) Effect of BSA binding on photophysical and photochemical properties of triarylmethane dyes. J. Phys. Chem. B 102, 4678-4688.
32. Docampo, R., S. N. J. Moreno, R. P. A. Muniz and R. P. Mason (1983) Light enhanced free radical formation and trypanocidal action of gentian violet (crystal violet). Science 220, 1292-1294.
33. Baptista, M. S. and G. L. Indig (1997) Mechanism of photobleaching of ethyl violet non-covalently bound to bovine serum albumin. Chem. Commun. 18, 1791-1792.
34. Weissig V. (2003) Mitochondrial-targeted drug and DNA delivery. Crit. Rev. Ther. Drug Carrier Syst. 20, 1-62.
35. Weissig, V., S. V. Boddapati, G. G. M. D'Souza and S. M. Cheng (2004) Targeting of low-molecular weight drugs to mammalian mitochondria. Drug Des. Rev. Online 1, 15-28.
36. Glaser M., S. K. Luthra and F. Brady (2003) Applications of positron-emitting halogens in PET oncology. Int. J. Oncol. 22, 253-267.
37. Pentlow, K. S., M. C. Graham, R. M. Lambrecht, F. Dagliglian, S. L. Bacharach, B. Bendriem, R. D. Finn, K. Jordan, H. Kalaigian, J. S. Karp, W. R. Robeson and S. M. Larson (1996) Quantitative imaging of iodine-124 with PET. J. Nucl. Med. 37, 1557-1562.
38. 125I) derivatives of rhodamine-123. J. Med. Chem. 30, 1757-1761.